The mechanism for nucleophilic substitution of α-carbonyl derivatives. Application of the valence-bond configuration mixing model

Journal of the Chemical Society, Perkin Transactions 2

Volumn , Issue 6, 1984, Pages 981-984

  McLennan, Duncan J ^a   Pross, Addy ^a,b  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b BEN GURION UNIVERSITY OF THE NEGEV   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049102919     PISSN: 1472779X     EISSN: None     Source Type: Journal    
DOI: 10.1039/P29840000981     Document Type: Article

References (40)

1. J. B. Conant, W. R. Kirner, J. Am. Chem. Soc., 1924, 46, 233.
2. J. B. Conant and R. E. Hussey, J. Am. Chem. Soc., 1925, 47, 476.
3. J. B. Conant W. R. Kirner, and R. E. Hussey, J. Am. Chem. Soc., 1924, 46, 233, J. B. Conant and R. E. Hussey, J. Am. Chem. Soc., p. 488.
4. J. B. Conant and R. E. Hussey, J. Am. Chem. Soc., p. 488.
5. A. Halvorsen and J. Songstad, J. Chem. Soc., Chem. Commun., 1978, 327.
6. S. Winstein, E. Grunwald, and H. W. Jones, J. Am. Chem. Soc., 1951, 73, 2700.
7. A. Streitwieser, ‘Solvolytic Displacement Reactions,’McGraw-Hill, New York, 1962, p. 28.
8. M. J. S. Dewar, ‘The Electronic Theory of Organic Chemistry,’Oxford University Press, Oxford, 1949, p. 73.
9. R. G. Pearson, S. H. Langer, F. V. Williams, and W. J. McGuire, J. Am. Chem. Soc., 1952, 74, 5130.
10. P. D. Bartlett and E. N. Trachtenberg, J. Am. Chem. Soc., 1958, 80, 5808.
11. J. W. Thorpe and J. Warkentin, Can. J. Chem., 1973, 51, 927.
12. W. Forster and R. M. Laird, J. Chem. Soc., Perkin Trans. 2, 1982, 135.
13. F. G. Bordwell and W. T. Brannen, J. Am. Chem. Soc., 1964, 86, 4645.
14. A. J. Sisti and S. Lowell, Can. J. Chem., 1964, 42, 1896.
15. S. S. Shaik, J. Am. Chem. Soc., 1981, 103, 3692.
16. A. Pross and S. S. Shaik, J. Am. Chem. Soc., p. 3702.
17. A. Pross and S. S. Shaik, J. Am. Chem. Soc., 1982, 104, 187.
18. A. Pross and S. S. Shaik, J. Am. Chem. Soc., p. 1129.
19. A. Pross and S. S. Shaik, J. Am. Chem. Soc., p. 2708.
20. S. S. Shaik, Nouv. J. Chim., 1982, 6, 159.
21. A. Pross, J. Org. Chem., in the press.
22. S. S. Shaik, J. Am. Chem Soc., 1983, 105, 4359.
23. For an alternative application of the CM model to π-acceptor substituents, S. S. Shaik, J. Am. Chem. Soc., 1981, 103, 3692.
24. A. Pross, Adv. Phys. Org. Chem., in the press.
25. A. Pross and S. S. Shaik, Acc. Chem. Res., 1983, 16, 363.
26. D. J. McLennan, J. Chem. Soc., Perkin Trans. 2, 1977, 298.
27. M. J. S. Dewar, ‘The Electronic Theory of Organic Chemistry,’Oxford University Press, Oxford, 1949, p. 25.
28. K. Murai, S. Takeuchi, and C. Kimura, Nippon Kagaku Zasshi, 1973, 95.
29. D. J. McLennan, Acc. Chem. Res., 1976, 9, 281.
30. J. -P. Bégué and M. Charpentier-Morize, Acc. Chem. Res., 1980, 13, 207.
31. D. Kost and K. Aviram, Tetrahedron Lett., 1982, 4157.
32. S. Wolfe, D. J. Mitchell, and H. B. Schlegel, Can. J. Chem., 1982, 60, 1291.
33. P. R. Young and W. P. Jencks, J. Am. Chem. Soc., 1979, 101, 3288.
34. R. F. Hudson and G. Klopman, J. Chem. Soc., 1962, 1062.
35. D. N. Kevill, J. Chem. Soc., Chem. Commun., 1981, 421.
36. E. M. Arnett and R. Reich, J. Am. Chem. Soc., 1980, 102, 5892.
37. A. Pross, D. J. De Frees, B. A. Levi, S. K. Pollack, L. Radom, and W. J. Hehre, J. Org. Chem., 1981, 46, 1693.
38. J. R. Jones, R. E. Marks, and S. C. Subba Rao, Trans. Faraday Soc., 1967, 63, 111.
39. D. J. McLennan, Tetrahedron, 1978, 34, 2331.
40. G. Baddeley and G. M. Bennett, J. Chem. Soc., 1935, 1819.